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Sheogorath has an old deal with Arch-Mage Shalidor in which the Vestige has to help Shalidor re-obtain all of his lorebooks that are not readable by Shalidor's own eyes due to a special enchantment that Sheogorath placed on the books out of entertainment.

This forces Shalidor to ask his assistant to translate the books for him at a slower pace. However, the books, little to Shalidor's knowledge were enchanted to drive his assistant "mad" resulting in a decision made by the Vestige at the end of the questline. The choice is a dozen Skyshards as a reward or a removal of the madness effect on the assistant, freeing her from her curse. If the choice is taking the Skyshards, Sheogorath will take the assistant with him back to the Shivering Isles.

In the final test, Sheogorath wants the Vestige to take a vacation in his family's chateau. However, all the three guest rooms are occupied, and two guests are cannibals. The correct guest is the one that isn't playing his role right and wants to get out. Next, the Vestige must find their way through a dark maze. Finally, they must fight their way through Madmen and Madwomen to a boss fight with Uncle Leo, a flesh atronach.

The Vestige and Shalidor journey to Eyevea, but Sheogorath left portals to Oblivion open and the island is covered in daedra. The Vestige fights Haskill. Sheogorath, who has been making Valaste slowly insane with his cursed books, offers to take her to the Shivering Isles. They can decide whether or not to save her.

"You made it this far, just as I had predicted. I am glad to see that my calculations were not in error. Now, if you are ready, we have a prison to break out of."

How did you wind up here?"I was captured shortly after Meridia pushed her city into this dread realm. This prison relies on darkness. Early on, I almost broke free. Now Molag Bal shapes the darkness itself to bind me, suppressing my attempts to escape."

So what should I do?"Molag Bal has trapped me within a pillar of darkness infused with his own vile energy and powered by the Light of Meridia. That, however, will be his undoing! The Light of Meridia can also banish this darkness, but you have to bring it to me."

I'm on my way."To reach me, you must first unlock the prison door. Molag Bal uses crystallized darkness to hold me and suppress my power. Move the crystals from their locations to the prison door and the way shall be opened for you."

Who are you, exactly?"I am the last Ayleid king. In our ancient language, my name means Ruler in Dark Times. I can imagine no darker time than the end of the Ayleid people."

How have you survived this long?"I am a servant of Meridia. Her master tactitian and strategist. Between my master's blessings and the time-distorting nature of this dread realm, I am alive. Consider that your good fortune, for you will never defeat Molag Bal without my help."

I'll bring the Light of Meridia to you."To reach me, you must first unlock this prison door. Molag Bal uses crystallized darkness to hold me and suppress my power. Move the crystals from their locations to the prison door and the way shall be opened for you."

"Let us not dawdle in this vile place. Find me in the Hollow City and speak to me there."

"I have barely set foot within these hallowed walls and I already feel a thousand times better! And now that you are here, we can determine our next move against the vile Molag Bal."

Do you have a plan?"I must take stock of our assets and resources. Determine just how much might we can bring to bear. Only then can I develop a strategy that shall allow us to win this war. But forgive me. I wanted to convey that you performed admirably at the tower."

"Well, if it isn't my old friend Hunts-For-Books! Now don't look so glum, or the skeevers'll notice. Then they hit you up for some spare gold, a few shin bones, your best pair of cheese-filled slippers. Insufferable beasts! They can't hold a conversation."

What do you want?"Mayor Aulus is a curd in the soup. A real fly in the whey, don't you say? Made a mess of me gift, the kind from the wrong end of a dog. I tried to encourage him. Even brought him a hero to destroy! But he couldn't go through with it. Can you imagine?"

You're talking about me."I led you right here to make it all boring again. And what did he do to stop you? Nothing! There I stood in my best old-lady suit, and he said it was all my fault! Ah, he just needs motivation. What better than an escaped prisoner seeking vengeance?"

You want me to kill him?"Could you kill someone you love? I can't! Well, I have. But not Mayor Aulus, it would be too pedestrian. No, I want you to try killing him."

Why should I try to kill him?"I want him to reach deep down, below all the marmalade and crushing failures defining his life, to find a seed of confidence, and grow it into a tree of gumption he'll use to beat your brains to paste. But if not, any brain paste'll do. Even his."

I'll do this if you swear to leave Southpoint forever."Deal! Oh, and one more thing. Daraneth stays behind. If you bore me too much, I'll turn her into a goose, roast her, and feed her to you covered in fine Eidar glaze. The goose, I mean. It's a might bit chilly for my Eidar-pants."